共查询到20条相似文献,搜索用时 31 毫秒
1.
A method has been developed for determining 3-mercaptohexan-1-ol (3-MH) in wine and grape juice using gas chromatography with conventional electron ionization (EI) mass spectrometry. The limit of quantitation of 40 ng/L was achieved with excellent precision using stable isotope dilution analysis (SIDA) combined with headspace solid-phase microextraction (SPME) of derivatized 3-MH. This method was used in combination with HPLC-MS/MS analysis of the individual diastereomers of 3-S-cysteinylhexan-1-ol (Cys-3-MH) and 3-S-glutathionylhexan-1-ol (Glut-3-MH), which are known precursors of the volatile thiol 3-MH. Commercial and small-lot winemaking trials were evaluated to determine the concentrations of precursors and free 3-MH at various stages of grape processing and winemaking. Five Sauvignon blanc clones were also assessed for precursors and free thiol during ripening, revealing the presence of 3-MH in the unfermented juices and a stark increase in precursor concentrations in the latter stage of ripening. Additionally, differences due to sample freezing and mode of juice preparation were revealed for the precursors, and a set of commercially available wines was analyzed to investigate the amounts of precursors and free 3-MH in Sauvignon blanc and other white wine varieties. There was seemingly no relationship between precursor concentrations in juice and 3-MH concentrations in wine. This was somewhat understandable, because the formation of precursors appears to be a dynamic process affected by a multitude of factors, beginning with grape ripening and continuing during vinification. 相似文献
2.
Formation of wine thiol precursors is a dynamic process, which can be influenced by vineyard and winery processing operations. With the aim of increasing thiol precursor concentrations, a study of the effects of storing machine-harvested Sauvignon blanc grapes prior to crushing and pressing was undertaken on a commercial scale. 3-Mercaptohexan-1-ol (3-MH) precursors, 2-S-glutathionylcaftaric acid (grape reaction product, GRP), glutathione (GSH) and a number of C6 compounds were assessed at several time points during the experiment. The concentration of the cysteine precursor to 3-MH doubled within 8 h and tripled after 30 h while the GSH and cysteinylglycine precursors increased in concentration roughly 1.5 times. (E)-2-Hexenal and GSH levels decreased as thiol precursors, GRP and C6 alcohols increased during storage. Principal component analysis revealed that precursors contributed to most of the variation within the samples over the storage period, with additional influence, primarily from GSH and GRP, as well as (E)-2-hexenal and (Z)-3-hexen-1-ol. Early storage time points were associated with higher concentrations of GSH and some unsaturated C6 compounds while longer storage times were most closely associated with higher thiol precursor and GRP concentrations. This study provides a detailed overview of interactions related to thiol precursor formation on a commercial scale and highlights the ability to manipulate precursor concentrations prior to grape crushing. 相似文献
3.
Capone DL Pardon KH Cordente AG Jeffery DW 《Journal of agricultural and food chemistry》2011,59(20):11204-11210
Precursors to varietal wine thiols are a key area of grape and wine research. Several such precursors, in the form of odorless conjugates, have been closely studied in recent years. A new conjugate has now been identified as 3-S-cysteinylglycinehexan-1-ol (Cysgly-3-MH), being the dipeptide intermediate between cysteine and glutathione precursors of tropical thiol 3-mercaptohexan-1-ol (3-MH). Authentic Cysgly-3-MH was produced via enzymatic transformation of the glutathione conjugate and used to verify the presence of both diastereomers of Cysgly-3-MH in Sauvignon blanc juice extracts. Cysgly-3-MH was added into our HPLC-MS/MS precursor method, and the validated method was used to quantify this new analyte in a selection of Sauvignon blanc juice extracts. Cysgly-3-MH was found in the highest concentrations (10-28.5 μg/L combined diastereomer total) in extracts from berries that had been machine-harvested and transported for 800 km in 12 h. This dipeptide conjugate was much less abundant than the glutathione and cysteine conjugates in the samples studied. On the basis of the results, the new cysteinylglycine conjugate of 3-MH seemingly has a short existence as an intermediate precursor, which may explain why it has not been identified as a natural juice component until now. 相似文献
4.
Dennis EG Keyzers RA Kalua CM Maffei SM Nicholson EL Boss PK 《Journal of agricultural and food chemistry》2012,60(10):2638-2646
Wine is a complex consumer product produced predominately by the action of yeast upon grape juice musts. Model must systems have proven ideal for studies of the effects of fermentation conditions on the production of certain wine volatiles. To identify grape-derived precursors to acetate esters, model fermentation systems were developed by spiking precursors into model must at different concentrations. Solid-phase microextraction-gas chromatgraphy mass spectrometry analysis of the fermented wines showed that a variety of grape-derived aliphatic alcohols and aldehydes are precursors to acetate esters. The C6 compounds hexan-1-ol, hexenal, (E)-2-hexen-1-ol, and (E)-2-hexenal are all precursors to hexyl acetate, and octanol and benzyl alcohol are precursors to octyl acetate and benzyl acetate, respectively. In these cases, the postfermentation concentration of an acetate ester increased proportionally with the prefermentation concentration of the respective precursor in the model must. Determining viticultural or winemaking methods to alter the prefermentation concentration of precursor compounds or change the precursor-to-acetate ester ratio will have implications upon the final flavor and aroma of wines. 相似文献
5.
Influence of grape-harvesting steps on varietal thiol aromas in Sauvignon blanc wines 总被引:1,自引:0,他引:1
Allen T Herbst-Johnstone M Girault M Butler P Logan G Jouanneau S Nicolau L Kilmartin PA 《Journal of agricultural and food chemistry》2011,59(19):10641-10650
The intense tropical fruit aroma of Sauvignon blanc wines has been associated with the varietal thiols 3-mercaptohexanol (3MH), derived from odorless precursors in the grape, and 3-mercaptohexyl acetate (3MHA), arising from 3MH during fermentation. Grapes and juice were sourced from five locations in Marlborough, New Zealand, taking hand-picked grapes and samples at four stages during the mechanical harvesting process and pressing, which were then fermented in replicated 750 mL bottles. With each set of juices, the highest concentrations of Cys-3MH and Glut-3MH were found in the juices pressed to 1 bar, but these juices produced wines with lower 3MH and 3MHA concentrations. With three of the juices, there was an increase in varietal thiol content for wines made from juices that had been machine harvested compared to the hand-picked samples, which matched earlier findings of lower 3MH and 3MHA levels in wines made from hand-picked grapes. Juices that were more oxidized, and which showed a higher absorbance at 420 nm, were found to produce wines with lower 3MH and 3MHA concentrations. 相似文献
6.
Subileau M Schneider R Salmon JM Degryse E 《Journal of agricultural and food chemistry》2008,56(19):9230-9235
The molar conversion yield of Cys-3MH into 3MH, during alcoholic fermentation, was traced using a deuterated isotope of the precursor added to different Sauvignon Blanc musts. This yield is close to that found in synthetic media supplemented with synthetic Cys-3MH, that is, below 1%. Yet, this represents only 3-7% of the total 3MH production in wine. This clearly shows that Cys-3MH is a precursor of 3MH, but not the main one in the different musts tested. The contribution of ( E)-hex-2-enal, which has been suggested as another potential precursor of 3MH, was discarded as well, as shown using also a deuterated analogue. The third suggested precursor of 3MH is a glutathionyl-3MH (G-3MH), which upon proteolytic degradation could release Cys-3MH. The knockout of the OPT1 gene, which encodes the major glutathione transporter, reduces 3MH accumulation by a 2-fold factor in grape must as compared to the wild type strain. Consequently, it is deduced that major 3MH precursor(s) are transported into yeast via Opt1p, which is in favor of G-3MH being a 3MH precursor. This work opens the search for the major natural precursor(s) of 3MH in Sauvignon Blanc must. 相似文献
7.
Thibon C Cluzet S Mérillon JM Darriet P Dubourdieu D 《Journal of agricultural and food chemistry》2011,59(4):1344-1351
Volatile thiols, compounds that contribute strongly to the varietal aroma, are present in much higher concentrations in sweet wines than in dry wines. This positive effect, due to the presence of Botrytis cinerea on the berries, in fact results from a strong enrichment of cysteine S-conjugate precursors in botrytized berries. In the present study, a convenient model was investigated to reproduce and therefore study this phenomenon. A Vitis vinifera cell culture was used as a simple model, and we focused on S-3-(hexan-1-ol)-l-cysteine (P-3SH), the cysteinylated precursor of 3-sulfanylhexanol. We demonstrated that grapevine cells were able to produce P-3SH and that the presence of B. cinerea considerably increased the precursor level (up to 1000-fold). This positive result was determined to be due to metabolites secreted by the fungus. These molecules were temperature sensitive, unstable over time, and their production was activated in the presence of grapevine cells. Moreover, part of the pathway leading to P-3SH was deciphered: it was directly derived from the cleavage of S-3-(hexan-1-ol)-l-glutathione, which itself was generated after a conjugation of glutathione on (E)-2-hexenal. 相似文献
8.
A mechanism for the formation of water-insoluble sediments in wines and juices made from red and white muscadine grapes (Vitis rotundifolia) was investigated as a function of processing methodology and storage. Sediments are considered quality defects in muscadine grape products, and their presence may influence consumer acceptability and expansion of retail markets. Processing regimes included both hot (70 degrees C) and cold (25 degrees C) press techniques for wine or juice production, and fermentations in contact with grape skins for 3, 5, and 7 days. Relationships between free ellagic acid (FE), total ellagitannins (ET), and total ellagic acid (TE) concentrations were evaluated initially in each product and in sediments that formed during storage for 50 and 120 days at 20 degrees C. Processing techniques influenced initial concentrations of these compounds and the extent of sediment formation. Following storage, juices generally had higher concentrations of FE in sediments compared to wines, but sedimentation was independent of initial FE or TE concentrations. Decreases in ET were observed for hot-pressed juice and skin-fermented wines after storage indicating their hydrolysis during storage and possible contribution to FE in sediments. However, quantitative analysis of the collected sediments revealed that no more than 12% FE by weight was actually present in the sediments, with the remainder consisting of either unidentified compounds or conjugated forms of ellagic acid. This work elucidated a potential mechanism for the presence of FE in muscadine wine and juice sediments through ellagitannin hydrolysis and suggests that sedimentation from mechanisms other than ellagic acid precipitation may also contribute to wine and juice quality. 相似文献
9.
Identification of volatile compounds in soybean at various developmental stages using solid phase microextraction 总被引:1,自引:0,他引:1
Boué SM Shih BY Carter-Wientjes CH Cleveland TE 《Journal of agricultural and food chemistry》2003,51(17):4873-4876
Soybean (Glycine max) seed volatiles were analyzed using a solid phase microextraction (SPME) method combined with gas chromatography-mass spectrometry (GC-MS). Thirty volatile compounds already reported for soybean were recovered, and an additional 19 compounds not previously reported were identified or tentatively identified. The SPME method was utilized to compare the volatile profile of soybean seed at three distinct stages of development. Most of the newly reported compounds in soybean seed were aldehydes and ketones. During early periods of development at maturity stage R6, several volatiles were present at relatively high concentrations, including 3-hexanone, (E)-2-hexenal, 1-hexanol, and 3-octanone. At maturity stage R7 and R8, decreased amounts of 3-hexanone, (E)-2-hexenal, 1-hexanol, and 3-octanone were observed. At maturity stage R8 hexanal, (E)-2-heptenal, (E)-2-octenal, ethanol, 1-hexanol, and 1-octen-3-ol were detected at relatively high concentrations. SPME offers the ability to differentiate between the three soybean developmental stages that yield both fundamental and practical information. 相似文献
10.
Peyrot Des Gachons C Tominaga T Dubourdieu D 《Journal of agricultural and food chemistry》2002,50(14):4076-4079
When Sauvignon blanc or Gros Manseng grape must was percolated through an immobilized gamma-glutamyltranspeptidase column, there was a significant increase in the concentration of S-3-(hexan-1-ol)-L-cysteine, the precursor of 3-mercaptohexan-1-ol, a compound that contributes to the varietal aroma of wines made from these grapes. Low- and high-resolution liquid secondary ion mass sepectrometry (LSIMS) analyses established the presence of S-3-(hexan-1-ol)-glutathione in Sauvignon blanc must. The identification of this compound suggests that the S-3-(hexan-1-ol)-L-cysteine in grapes is produced by the catabolism of S-3-(hexan-1-ol)-glutathione. As is the case in other plant or animal organisms, S-glutathione conjugates may be involved in certain detoxification systems in vines. 相似文献
11.
Three olfactometric methods (frequency of detection, time--intensity method, and aroma extract dilution analysis) were used to evaluate the main odorants of three musts obtained from French--Romanian hybrids (Valerien, Admira, and Brumariu). The three methods allow detection of the same odor-active compounds. The results obtained from these methods were closely related. Nineteen odor-active compounds were detected, and 13 were identified. The three methods showed the importance of an unidentified compound with a grape and grape juice aroma note in the three musts. Among the other compounds, 3-hexen-1-al, (E,Z)-2,6-nonadien-1-ol, and 1-ccten-3-one seemed to contribute actively to the odor of Valerien must. 3-(Methylthio)propanal and hexanal were contributors to the Admira and Brumariu odor. Phenylacetaldehyde was one of the main odor-active compounds in must from Admira. 相似文献
12.
The development of a method for assaying S-3-(hexan-1-ol)-L-cysteine, the cysteinylated precursor of 3-mercaptohexan-1-ol (P-3MH), in must has made it possible to study its impact on the aromatic potential of Merlot and Cabernet Sauvignon grape varieties used to produce rose wines in Bordeaux. The original feature of this method is the purification of very small volumes of must (500 microL) containing P-3MH by affinity chromatography and gas-phase chromatography coupled with mass spectrometry of the purified precursor in trimethylsilylated derivative form. Assays of the cysteinylated precursor in Merlot and Cabernet Sauvignon grapes showed that it was mainly located in the grape skins (60%). Prolonged juice-skin contact increased the must's P-3MH content, and this phenomenon was more marked at higher temperatures. Assessment of the aromatic potential of must used to produce rose wines by chemical analysis of an S-cysteine conjugate is mentioned for the first time. 相似文献
13.
Maggu M Winz R Kilmartin PA Trought MC Nicolau L 《Journal of agricultural and food chemistry》2007,55(25):10281-10288
14.
Carrapiso AI Jurado A Timón ML García C 《Journal of agricultural and food chemistry》2002,50(22):6453-6458
The odor-active compounds of different commercial types of Iberian hams (Montanera and Pienso) were researched by gas chromatography-olfactometry based on a detection frequency method. The hams (long- and short-Montanera and Pienso Iberian hams) showed different sensory profiles, differences being significant for Montanera ham typical odor, aroma intensity and persistence, and cured and moldy aroma. Significant differences were also found for some odorants. The largest differences appeared in 2-acetyl-1-pyrroline, hexanal, (Z)-3-hexenal, ethyl 2-methylbutyrate, (E)-2-hexenal, 1-octen-3-one, 1-octen-3-ol, 2-propionyl-1-pyrroline, octanal, and an unknown odorant. Sensory characteristics and olfactometric profiles were significantly different between Montanera and Pienso hams. Significant differences also appeared between long- and short-Montanera hams, which shows great variability in this commercial type. Otherwise, the largest scores for moldy aroma in long-Montanera hams matched with the largest detection frequency of 1-octen-3-one and 1-octen-3-ol in this group. 相似文献
15.
All eight C6-aliphatic alcohol and aldehyde compounds in naturally occurring green leaves showed bacteriostatic effects against Staphylococcus aureus IFO 12732, methicillin-resistant S. aureus, Escherichia coli IFO 3301, E. coli O157:H7, and Salmonella enteritidis, with bacteriostatic activities of less than 12.5 microg mL(-1). In this study, the susceptibility of Gram-positive bacteria tested was observed to be greater than that of Gram-negative bacteria. The bactericidal action of the aldehyde compounds was found to be much stronger than that of the alcohol compounds under both liquid and gaseous conditions. The most effective compound was (3E)-hexenal at concentrations of 0.1 and 1 microg mL(-1), which killed 2.1 x 10(5) cfu mL(-1) of S. aureus IFO 12732 and 1.4 x 10(5) cfu mL(-1) of E. coli IFO 3301, respectively, by direct contact with the compound. Lethality of (3E)-hexenal against S. aureus IFO 12732 and E. coli IFO 3301 was also observed as a result of gaseous contact at concentrations of 3 and 30 microg mL(-1), respectively. The bactericidal effects of 30 microg mL(-1) (3E)-hexenal were thoroughly maintained throughout periods of 2 days and 1 day against S. aureus IFO 12732 and E. coli IFO 3301, respectively, by a complex formation with alpha-cyclodextrin. 相似文献
16.
Volatile substances of Callicarpa japonica Thunb. were examined for their antibacterial activities against six foodborne microorganisms using the optical densitometer Bioscreen C. Extracts of C. japonica were obtained by simultaneous steam distillation and solvent extraction (SDE), and those extracted for 1.5 and 2.0 h at pH 6.0 strongly inhibited the growth of Bacillus cereus and Salmonella typhimurium; the content of the volatile substances of leaves at these pH levels were 543.1 and 706.7 mg/kg, respectively. All foodborne microorganisms tested were strongly inhibited by the addition of >8% (v/v) of the SDE extracts to broth medium. The major volatile components of the SDE extracts obtained at 1.5 h and pH 6.0 were gamma-caryophyllene, 1-octen-3-ol, 2-hexenal, germacrene B, and aromadendrene II, with corresponding peak areas of 44.14, 15.6, 9.86, 5.24, and 4.01%, respectively, and major antibacterial components were 1-octen-3-ol and 2-hexenal. Among the 32 materials identified as volatile flavor components, 2-hexenal, 2,4-hexadienal, 1-octen-3-ol, 2,4-heptadienal, and epiglobulol strongly inhibited microorganism growth. In particular, 2-hexenal (107.52 mg/L) and 1-octen-3-ol (678.64 mg/L) inhibited the growth of most microorganisms tested by >90%. 相似文献
17.
Singletary KW Stansbury MJ Giusti M Van Breemen RB Wallig M Rimando A 《Journal of agricultural and food chemistry》2003,51(25):7280-7286
The effects of Concord grape juice constituents on the promotion of chemically induced rat mammary tumor development and on the proliferation of a rat mammary adenocarcinoma cell line were studied. Isocaloric grape juice formulations provided in the drinking fluid of rats at concentrations of 489 and 651 mg of phenolics/dL of fluid significantly inhibited mammary adenocarcinoma multiplicity compared to controls. Final tumor mass also was significantly decreased for animals provided these two grape juice concentrations compared to controls. In addition, DNA synthesis of the rat mammary adenocarcinoma RBA cell line was significantly inhibited in a dose-dependent manner for cells treated with a grape extract, with an IC50 dose of approximately 14 micrograms of phenolics/mL. This inhibition of DNA synthesis was not accompanied by changes in 8-oxodeoxyguanosine formation or by substantial cell cycle arrest. These studies thus indicate that Concord grape juice constituents can inhibit the promotion stage of 7,12-dimethylbenz[a]anthracene (DMBA)-induced rat mammary tumorigenesis, in part by suppressing cell proliferation. 相似文献
18.
Kalua CM Allen MS Bedgood DR Bishop AG Prenzler PD 《Journal of agricultural and food chemistry》2005,53(20):8054-8062
Olive oil and fruit samples from six cultivars sampled at four different maturity stages were discriminated into cultivars and maturity stages. The variables-volatile and phenolic compounds-that significantly (p < 0.01) discriminated cultivars and maturity stage groups were identified. Separation by stepwise linear discriminant analysis revealed that Manzanilla olive cultivar was separated from cultivars Leccino, Barnea, Mission, Corregiola, and Paragon, whereas cultivars Corregiola and Paragon formed a cluster. The volatile compounds hexanol, hexanal, and 1-penten-3-ol were responsible for the discrimination of cultivars. All maturity stages were discriminated, with the separation of early stages attributed to oil phenolic compounds, tyrosol and oleuropein derivatives, whereas the volatile compounds (E)-2-hexenal, hexanol, 1-penten-3-ol, and (Z)-2-penten-3-ol characterized the separation of all maturity stages and in particular the late stages. Hexanol and 1-penten-3-ol characterized the separation of both cultivars and maturity stages. 相似文献
19.
20.
Green leaf volatiles (GLVs) from Brassica oleracea subsp. capitata L. have been identified as 1-hexanol, (Z)-3-hexen-1-ol, 1-hexen-3-ol, hexanal, (E)-2-hexenal, hexyl acetate, and (Z)-3-hexenyl acetate, by their mass spectra and retention times in comparison with authentic samples. No isothiocyanates were found in the extract. The activity of these chemicals has been determined on mated and unmated males and females of the diamondback moth (DBM) Plutella xylostella in the laboratory (wind tunnel) and in the field. On unmated males, mixtures of (Z)-3-hexenyl acetate, (E)-2-hexenal, and (Z)-3-hexen-1-ol with the pheromone induced attractant/arresting behavior in 80-100% of the males tested, significantly higher than the effect induced by the pheromone alone. On mated males and unmated females the effect of the GLVs alone or in combination with the pheromone was poor, while on mated females these compounds elicited upwind flight and arresting behavior in 40-60% of the females assayed. There was no synergism when these chemicals were mixed with the pheromone. In the field, (Z)-3-hexenyl acetate, the most active GLV in laboratory tests, when mixed with the pheromone in 1:1 ratio, enhanced 6-7-fold the number of females and 20-30% the number of males caught by traps over those baited with the pheromone alone. Our results indicate that the enhancement of the attraction of both males and females of the DBM to traps baited with pheromone blended with the relatively inexpensive and environmentally safe (Z)-3-hexenyl acetate may be important for future control strategies of the pest. 相似文献